The Worst Decision Tony Ever Made As Boss On The Sopranos

Over six stellar seasons of The Sopranos, viewers got to see Tony (James Gandolfini) deal with a lot of complex issues. Tony's problems sometimes come from an outside source, such as the long-running FBI investigation into his criminal empire. Others come from within, like Tony's constant struggles with blood relatives, like his sister Janice (Aida Turturro) and his mother Livia (Nancy Marchand).

However, some of the most interesting conflicts on The Sopranos come someplace in the middle — from the extended network of associates who make up Tony's crew. While the characters in the show supposedly all live by a code of conduct as made men, The Sopranos' true genius was its understanding that each character has their own motivations and instincts, which rarely line up. As a result, many of the plotlines revolve around Tony's management of his organization. The Soprano crime family is one big HR disaster, to be frank.

The Sopranos goes to great lengths to give viewers an idea of how Tony makes his choices as he seeks to consolidate his power and control his empire. While he makes a lot of solid decisions, he also makes a few mistakes. Here is the worst decision Tony ever made as boss on The Sopranos.

One of the show's most significant challenges to Tony's leadership comes with the arrival of Ralphie Cifaretto (Joe Pantoliano). In the third season of The Sopranos, Ralphie returns from his long exile in Florida with ambitious plans to make his mark in New Jersey. His reemergence quickly becomes an issue for Tony, who understands that Ralphie, while a solid earner for the family, is uncontrollable and prone to acts of sudden violence.

Tony and Ralphie's friction comes to a head halfway through the third season, after Ralph kills Tracee (Ariel Kiley) outside of Silvio Dante's (Steven Van Zandt) nightclub, Bada Bing. Tony attacks Ralphie, which violates the code of their organization, as Ralphie is a made man. To make amends for his actions, Tony is forced to promote Ralphie to the position he wants, as captain of the Aprile crew.

Once in position as a leader in the organization, Ralphie can wield his new influence to make Tony's life even more difficult, which he promptly does by starting up a relationship with Tony's sister, Janice.

While certainly a misstep, the instance of Tony's losing his temper and being forced to reward the volatile Ralphie wasn't his crucial mistake. That came a little bit later, in The Sopranos' fourth season.

Early in season 4, Ralphie insults the wife of the head of the New York crime family, Johnny Sac (Vincent Curatola), by making a joke about her weight. As the season continues, Johnny becomes increasingly furious about the slight, and eventually calls a meeting to demand that he be allowed to put a hit out on Ralphie. Tony refuses to allow it, despite his misgivings about having Ralphie in his organization.

While protecting a member of his crew from another seems like a reasonable action, Tony and Ralphie's problems would come to a violent end just a few episodes later. While Tony survives that incident, the mysterious circumstances of Ralphie's death follow Tony to the end of the show. Killing a made man undermines the entire structure of trust in Tony's criminal organization, whereas allowing Johnny Sac to put out a hit on Ralphie would have taken the issue off Tony's already full plate.